The document discusses carbohydrates and their classification. It notes that carbohydrates include monosaccharides, disaccharides, oligosaccharides, and polysaccharides. Monosaccharides can be further classified as aldoses or ketoses depending on whether they have an aldehyde or ketone functional group. Common monosaccharides include trioses, tetroses, pentoses, and hexoses. Disaccharides are formed from the condensation of two monosaccharide units and include maltose, sucrose, and lactose. Polysaccharides are formed from the condensation of many monosaccharide units and can be homopolysaccharides or heteropolysaccharides.
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Chemistry of carbohydrates and their structure
1.
2. Aldehyde or Ketone derivatives of polyhydroxy
alcohols.
General formula
(CH2O)n
3. Most abundant bio molecules.
Main source of energy (4 kcal/gm) .
Absolutely required for RBCs’ & brain cells.
Storage form of energy i.e. starch & glycogen.
Required for oxidation of fats.
Excess CHO are converted into fats.
Glyco protein & Glyco lipids are components of
cell membrane.
Structural basis of many organisms.
Used as drugs i.e. antibiotics & cardiac
Glycosides.
22. Colorless, crystalline solids , sweet taste, water
soluble compounds.
Aldoses
Ketoses
Poly Hydroxy alcohols i.e. having (OH-) groups
Depending upon the no. of (OH-) groups, they
contain one or more centre of Asymmetry, which
affects their optical & biological activity.
23. Dihydroxy acetone (ketotriose) is an exception,
(does not have any asymmetric carbon).
Glyceraldehyde (aldotriose) is called as the
“REFERENCE SUGAR”.
Carbonyl carbon
Asymmetric carbon
24. ISOMERISM IN MONOSACCHARIDES
1. Stereo isomerism
2. Enantiomers
3. D & L isomers
4. Optical isomers
5. Aldose-Ketose isomers
6. Anomers
7. Epimers
8. Pyranose & Furanose isomers
25. 2 or more Monosaccharides having same formula, but
differing from each other in structural configuration i.e.
spatial arrangement of H or OH atoms in their structure.
26. 4 different groups attached to the same carbon .
Parent compound (reference molecule) is
Glyceraldehyde (1 asymmetric C).
27.
28. In general a molecule with n chiral center can have 2n
stereo isomers.
Glyceraldehyde 21
Glucose 2 4
29. ENANTIOME
RS
These are mirror
images of each other.
They form D & L
isomers.
All mono saccharides
can be considered to
be derived from
Glyceraldehyde.
30.
31. The configuration of H & OH groups at the second
Carbon atom of Glyceraldehyde forms D & L sugars.
Penultimate carbon atom is the reference carbon for
naming D & L mirror images.
32. Non super imposable complete mirror images,
differ in configuration at every chiral center.
In D form OH group is on the RIGHT , while
in L form OH group is on the LEFT of the chiral
carbon.
D & L isomers differ from each other by orientation
around PENULTIMATE CARBON
(C -5 in case of Glucose molecule)
,farthest from the carbonyl(C= O)carbon.
Human body can metabolize D-sugars only.
Naturally occuring sugars are D-sugars except
L-Arabinose .
33.
34. Presence of asymmetric C atom confers optical
activity to the carbohydrates.
When a beam of plane polarized light is passed
through a carbohydrate solution
It will rotate the light either
to right DEXTRO ROTATORY(+)
to left LEVO ROTATORY (-)
35. The direction of rotation of plane polarized light is
independent of the stereo-chemistry of sugar.
Sugar may be designated as,
D(-) ,D(+) or L(-) ,L(+)
Naturally occuring form of Fructose is D but it is
levo rotatory. i.e. ( D-)
Glucose is D sugar, but dextro rotatory i.e. (D+)
36. Plane polarized light does not rotate to right or left,
if
Compound does not possess plane of asymmetry.
Equal amounts of dextro or levo isomers are
present RECEMIC MIXTURE.
Meso compounds having asymmetric carbon but
due to internal compensation i.e. Meso tartaric
acid.
37. Sugars that differ only in the configuration
around one Carbon atom (other than
reference carbon).
38.
39.
40.
41. Cyclic structures are formed by the reaction
between an ALDEHYDE/KETONE group and a
HYDROXYL group in a monosaccharide with 5 or
more carbon atoms.
Cyclic structure is thermodynamically favored and accounts for many properties of
mono -saccharides
42. The open chain form (FISCHER PROJECTION) is
found in < 0.1% of the molecules in an aqueous
solution.
An intra molecular reaction in which one of the OH
group of the sugar is added to the Aldehyde/ Ketone
group of the same molecule ---- forms a cyclic
structure.
The cyclic (ring) structure is called -----------
HAWORTH PROJECTION.
The carbonyl carbon(C-1 of Aldose /C-2 OF KETOSE)
in ring structure is called ANOMERIC CARBON
43.
44.
45.
46.
47.
48.
49. Condensation between Ketone group and a OH group
forms the hemi Ketal linkage.
Condensation between the Aldehyde/Keto group is in
1:1.
As a result of these linkages ANOMERIC CARBON
gives an additional asymmetric carbon.
Depending upon the configuration, OH group are found
above or below the ring.
OH group on the right in Fischer projection appear under
the ring in Haworth projection ,while those on the left are
above the ring.
50. OH group at C-5 / C-6 reacts with the Keto group
at C-2, forming a FURANOSE/PYRANOSE cyclic
structure having a hemi Ketal linkage.
D-Fructose readily forms the Furanose ring.
Common anomer of Fructose is the β - D
Fructose.
51.
52. In Aldohexoses the OH group at C-5 reacts with the
c=o group and forms a six member
ring---PYRAN RING .
Sugars having this ring are called PYRANOSES.
If the OH group at C-4 reacts, a five member ring---
FURAN RING is formed &
Sugars are called FURANOSES.
OH group to the right is below the plane----α
Oh group to the left is above the plane of symmetry---
β
53.
54.
55. Anomeric carbon by giving an additional chiral
carbon makes the total isomers 25. (32)
Anomeric carbon gives 2 stereo isomers i.e.
α & β ANOMERS .
α & β forms are not Enantiomers.
They differ only in respect to configuration around
Anomeric carbon.
They are present only in cyclic form, & do not
show the Aldehyde group normally present in
Glucose.
Ring structure is also called AMYLENE OXIDE .
56. In Glucose solution ,2/3 of sugar exist as β form,&
1/3 as α form.
Inter conversion of α & β forms is called
MUTA ROTATION .
In the solution there is opening of Hemiacetal ring
to form traces of Aldehyde sugar & then Re
condensation to the cyclic form.
57.
58.
59. When plane polarized light is passed through a Molar
solution of D- Glucose, Its specific rotation keeps on
changing
α- D Glucose in the solution shows --+112˳ while β-
Glucose shows ---- +19˳. After a
certain period of time two forms reach at an end point----
+19˳.
Mutarotation leads to an equilibrium between α & β forms
in which 62% of the molecules are present in the β form ,
while 38% in the α form.
a
60.
α & β Anomers can be obtained in pure forms.
It is possible to determine the sugar content of
different beverages.